[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].CCN(CC)CC.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:23]([Si:26]([CH3:28])([CH3:27])[O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14])([CH3:25])([CH3:24])[CH3:22]
To a well-stirred solution of 7-Hydroxy-6-methoxy-1-tetralone (80.0 mg, 0.42 mmol) in CH2Cl2, was added Et3N (47 mg, 0.46 mmol), followed by DMAP (5.1 mg, 0.042 mmol) and TBSCl (69 mg, 0.46 mmol) at 0° C. under dry nitogen. After 2 h (at rt), the mixture was partitioned between CH2Cl2 and water. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 7-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone (122 mg, 0.40 mmol, 95%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 0.15 (s, 6H), 0.99 (s, 9H),2.11 (m, 2H), 2.58 (t, J=6.1 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 3.86 (s, 3H), 6.63 (s, 1H), 7.56 (s, 1H).
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